Ethyl Acetate → HCID 131734930, compound

HRID 921551Notes

Reaction equation

HRID 921551 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:17]([C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][C:27]=2[C:29]2[CH:30]=[N:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)[NH:22][N:21]=1)([CH3:19])[CH3:18].C(OCC)(=O)C>CN(C=O)C.O>[CH:17]([C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][C:27]=2[C:29]2[CH:30]=[N:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:22]([C:4]2[C:3]([CH3:10])=[CH:2][CH:9]=[CH:8][C:5]=2[C:6]#[N:7])[N:21]=1)([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27791804-Fluoro-3-methylbenzonitrileHCID 178440423HCID 178440423, compound

Product 1

HCID 131734930HCID 131734930, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluoro-3-methylbenzonitrile (0.077 g) and cesium carbonate (0.203 g) were added to a solution of compound (6c) (0.150 g) in DMF (1.73 mL), followed by stirring at 80° C. for 18 hr. The reaction solution was distributed between ethyl acetate and water. The organic layer was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain 4-{(3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile (0.154 g, 73%). This 4-{3-isopropyl-4-(quinolin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl}-3-methylbenzonitrile was dissolved in DMSO (5.0 mL) and ethanol (5.0 mL). A 4 N aqueous sodium hydroxide solution (0.195 mL) and a 30% hydrogen peroxide solution (0.088 mL) were added to the resulting solution, followed by stirring at room temperature for 30 min. Water was added to the reaction solution, and the precipitate was collected by filtration, washed with diethyl ether, and dried under reduced pressure to obtain compound (80) (0.135 g, 83%) as a white solid.

Workup

  1. washThe organic layer was washed with saturated saline
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away
  4. customthe residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2f66d82bbb044ad18020386c8878f3cd
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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